List of reactions in organic chemistry

This list is intended to provide an overview of the most important chemical reactions in organic chemistry according to the classification of the resulting bond types and standard building blocks.

CC single bond

• Grignard reaction (addition of halogenated organomagnesium compounds of the structure to carbonyl groups)
• Ortho-metalation (metalation of correspondingly substituted aromatics with alkyllithium compounds)
• Negishi coupling (conversion of aryl halides or triflates in a nickel or palladium-catalyzed reaction with organozinc compounds)
• Acyloin condensation (condensation of two esters to form α-hydroxycarbonyl compounds)

C = C double bond

• Wittig reaction (conversion of phosphorylides with carbonyl compounds)
• Horner-Wadsworth-Emmons reaction (reaction of aldehydes or ketones with the anions of organic phosphonates)
• Peterson olefination
• Olefin metathesis
• Aldol condensation (reaction of aldehydes or ketones catalyzed by acids or bases with subsequent elimination of water)

Alcohols

From reactions with double bonds

• Hydrolysis of C = C double bonds with water or oxymercuration , Markovnikov product
• Hydrogenation of C = C double bonds with boranes , Anti-Markovnikov
• Hydrogenation of C = O double bonds with chiral boranes, e.g. B. Alpine borane

Vicinal diols

• Oxidation of C = C double bonds with alkaline potassium permanganate solution or osmium tetroxide , cis- diol
• Oxidation of C = C double bonds with peracids and subsequent hydrolysis, trans-diol

From reduction of aldehydes / ketones / carboxylic acids

• Corey-Fuchs reaction from aldehydes

3 rings

Cyclopropanes

• Cheletropic reaction ([2 + 1] addition of a carbene to an olefin )
• 1,3-dibromoalkane with magnesium (Grignard reaction)

Oxiranes

• Oxidation of olefins with peracids (e.g .: meta-chloroperbenzoic acid )
• Stereoselective epoxidation with tert -butyl hydroperoxide with the aid of diethyl tartrate ( Sharpless epoxidation )

4 rings

Cyclobutane Syntheses

• (2 + 2) Cycloaddition of Olefins

Oxetanes

• Paternò-Büchi reaction (2 + 2 cycloaddition of an olefin with a carbonyl compound)

5 rings

Cyclopentanes

• 1,3-dipolar cycloaddition

Cyclopentenones

Pauson-Khand reaction (reaction of an alkyne , alkene and carbon monoxide )

3-thiazolines

• Asinger reaction

6 rings

Cyclohexenones

• Robinson annulation ( Michael addition , then aldol reaction )

Cyclohexenes

• Diels-Alder reaction (4 + 2 cycloaddition)

benzene

• Vollhardt cyclization
• 3-fold aldol condensation
• Diels-Alder reaction 4 + 2 cycloaddition with alkynes

Dicarbonyl compounds

1,2-dicarbonyl compounds

• Riley oxidation

1,3-dicarbonyl compounds

• Claisen condensation

1,4-dicarbonyl compounds

• Stetter reaction
• Corey-Seebach reaction in a Michael system

1,5-dicarbonyl compounds

• Michael addition (addition to an α, β-unsaturated carbonyl compound with a soft nucleophile)

1,6-dicarbonyl compounds

• Cyclopropane trick (Michael addition of a carbonyl compound to a cyclopropene homo system)
• Ozonolysis of a cyclic olefin